One-Pot Synthesis of Structurally Diverse Iminosugar-Based Hybrid Molecules

A one-pot iminium-ion-based
strategy has been developed for the
synthesis of structurally novel iminosugar-based hybrid molecules.
Iminium ion derived from l-rhamnose lactol-mesylate reacted
with electron-rich aromatic systems in an inter/intra molecular fashion
to furnish pyrrolidine-based iminosugar C-aryl glycosides
with a high degree of stereoselectivity. Iminium ion also reacted
readily with active methylene compounds such as 4-hydroxycoumarin,
4-hydroxyquinolinone, and lawsone to provide iminosugar C-coumarin/quinolinone/naphthoquinonyl glycosides in very good yields.
Azomethine ylide generated from an iminium ion derivative underwent
dipolar cycloaddition reaction with 1,4-quinones to furnish novel
isopyrrolonaphtho/anthroquinon-based iminosugar-hybrids. The preliminary
cytotoxic activities of some of the synthesized iminosugar-hybrids
have been assayed against various human cancer cell lines and some
of the hybrid molecules exhibited promising anticancer activities.